Английская Википедия:8-Hydroxyquinoline
8-Hydroxyquinoline (also known as oxine) is an organic compound derived from the heterocycle quinoline. A colorless solid, its conjugate base is a chelating agent, which is used for the quantitative determination of metal ions.
In aqueous solution 8-hydroxyquinoline has a pKa value of ca. 9.9[1] It reacts with metal ions, losing the proton and forming 8-hydroxyquinolinato-chelate complexes.
The aluminium complex,[3] is a common component of organic light-emitting diodes (OLEDs). Substituents on the quinoline ring affect the luminescence properties.[4]
In its photo-induced excited-state, 8-hydroxyquinoline converts to zwitterionic isomers, in which the hydrogen atom is transferred from oxygen to nitrogen.[5]
Bioactivity
The complexes as well as the heterocycle itself exhibit antiseptic, disinfectant, and pesticide properties,[6][7] functioning as a transcription inhibitor.[8] Its solution in alcohol is used in liquid bandages. It once was of interest as an anti-cancer drug.[9]
A thiol analogue, 8-mercaptoquinoline is also known.[10]
The roots of the invasive plant Centaurea diffusa release 8-hydroxyquinoline, which has a negative effect on plants that have not co-evolved with it.[11]
See also
- Nitroxoline (5-nitro-8-hydroxyquinoline), an antiprotozoal drug
- PBT2
- QUPIC
- Ionophore
- Trace metal detection test
References
Шаблон:Antiseptics and disinfectants Шаблон:Gynecological anti-infectives and antiseptics Шаблон:Antiprotozoal agent
aluminium(III)-from-xtal-2000-CM-3D-ellipsoids.png){kind=link}